2-[(3-Methoxyphenyl)methyl]-2,3-dihydro-1H-inden-1-one

Base Information

• Chemical Name: 2-[(3-Methoxyphenyl)methyl]-2,3-dihydro-1H-inden-1-one
• CAS No.: 13578-99-9
• Molecular Formula: C17H16O2
• Molecular Weight: 252.313
• DSSTox Substance ID: DTXSID10530949
• Mol file: 13578-99-9.mol

Synonyms:13578-99-9;2-[(3-Methoxyphenyl)methyl]-2,3-dihydro-1H-inden-1-one;DTXSID10530949;AKOS011019211

Chemical Property of 2-[(3-Methoxyphenyl)methyl]-2,3-dihydro-1H-inden-1-one

Chemical Property:

• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 252.115029749
• Heavy Atom Count: 19
• Complexity: 325

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=CC(=C1)CC2CC3=CC=CC=C3C2=O

Technology Process of 2-[(3-Methoxyphenyl)methyl]-2,3-dihydro-1H-inden-1-one

There total 8 articles about 2-[(3-Methoxyphenyl)methyl]-2,3-dihydro-1H-inden-1-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

tert-butyl (2-allylbenzoyl)(benzyl)carbamate + 3-methoxyphenylboronic acid pinacol ester (325142-84-5) → 2-(3-methoxybenzyl)-2,3-dihydro-1H-inden-1-one (13578-99-9)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; potassium phosphate; 1,3-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene; In tetrahydrofuran; water; at 60 ℃; Inert atmosphere;

DOI:10.1021/jacs.7b06191

Reference yield: 65.0%

2-allyl benzoic acid methyl ester (61463-59-0) + 3-methoxyphenylboronic acid (10365-98-7,1107579-37-2) → 2-(3-methoxybenzyl)-2,3-dihydro-1H-inden-1-one (13578-99-9)

Guidance literature:

With 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazolium tetrafluoroborate; potassium fluoride; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; potassium tert-butylate; cesium fluoride; In tetrahydrofuran; at 80 ℃; for 16h; Inert atmosphere; Sealed tube;

DOI:10.1002/anie.201911372

Reference yield:

inden-1-one (83-33-0) + 3-methoxy-benzaldehyde (591-31-1) → 2-(3-methoxybenzyl)-2,3-dihydro-1H-inden-1-one (13578-99-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / ethanol / 0.5 h / 20 °C

2: formic acid; triethylamine; C₁₈H₂₄ClIrN₃⁽¹⁺⁾*Cl^(1-) / water / 6 h / 80 °C / Green chemistry

With formic acid; C₁₈H₂₄ClIrN₃⁽¹⁺⁾*Cl^(1-); triethylamine; sodium hydroxide; In ethanol; water;

DOI:10.1016/j.tetlet.2021.153627

upstream raw materials:

3-methoxyphenylboronic acid pinacol ester

2-Iodobenzoic acid

N-benzyl-2-iodobenzamide

2-Iodobenzoyl chloride

Downstream raw materials:

2.2-Bis-(m-methoxy-benzyl)-1-indanon

(R)-N-(2-fluoro-2-(3-methoxybenzyl)-2,3-dihydro-1H-inden-1-ylidene)benzamide